Rhett Butler of Gone with the Wind is a pretty Bad Ass guy who's known for fighting, messing with loads of girls and general illegal stuff. He also reads Shakespeare, always knows the latest fashion trends, comforts his daughter when she gets scared of the dark, and often chats with women about parenthood. This book actually lampshades the fact that no one wants to confront Rhett over his 'sensitive' traits because he's so Bad Ass.
He also takes the opinions of women seriously, treats them as thinking beings, and isn't afraid to ask them for advice. By the standards of the time, this makes him very effeminate- any man who didn't consider himself superior to women was thought by other men to be weak and ridiculous.
Ashley may also count. He's a quiet, poetry-reading intellectual who believes that War Is Hell (and gets shouted at by other men for this), but he readily decides to fight in the war and joins the Klu Klux Klan. (Again, Deliberate Values Dissonance.)
In Captain Underpants, the school football team are such fans of Barney Captain Ersatz Boomer the Purple Dragon that they change their team name to the Purple Dragon Sing-Along Friends. As the author points out, who's going to argue with a bunch of linebackers?
Butler, a hulking Badass Normal and Battle Butler in Artemis Fowl, claims to only enjoy reading soppy romance novels — apparently, books with action and explosions and helicopters and stuff like that remind him too much of real life.
Discworld is full of people who fulfill this trope.
In The Truth, Mr. Tulip is a giant bruiser who can barely think, whose every second word is "—ing" (literally) and whose brain is constantly fizzing with what he thinks are awesome drugs, but show him any antique or work of art and he'll be able to instantly identify the period, creator, history and technique, as well as whether or not the particular example is genuine or a copy, and will often burst into tears because of how —ing beautiful it is.
In Unseen Academicals, the Dimwell fan colours are bright pink and green. Nutt theorizes that they're a deliberate attempt to pick a fight.
Captain Carrot Ironfounderson, a six-foot tall Dwarf, has all the typical Dwarf traits: a dedication to polishing his armour, a great admiration of all forms of craftsdwarfship (from bakery to jewellery to the latest in fashion), and enough upper body strength to drive his sword through the Big Bad and right through the three feet thick marble pillar behind him. More uniquely "Carrot" traits involve starting a youth football club (among the violent street gangs of the world's worst ghetto), setting up a "volunteer" scheme to do things for the elderly (the "volunteer" helpers are convicted murderers on a community service scheme) and arresting the rulers of Ankh-Morpork several times (including the Dragon who took over the city and the head Thief of the Thieves' guild).
Oh, and one time he tried to arrest Vetinari himself.
For parking improperly. Because Carrot is the only person who's read the laws of Ankh-Morpork.
Although the time he arrested the head thief was an accident; he was new to the city, and once they explained the Guild system to him there was no more trouble with it.
Wee Mad Arthur, a three-inch-tall Feegle raised by gnomes who loves ballet, opera and visiting art galleries and can beat up half-a-dozen regular Nac Mag Feegle single handed. He also terrifies full-sized humans, and anyone who tries to step on him never tries it twice.
In Witches Abroad Nanny Ogg mentions that her gigantic hulking barge of an eldest son, the town blacksmith Jason Ogg, knits socks in the evenings. Of course, he's still, you know, a guy with minivans where his biceps oughta be; the socks he knits are made with the super-tough wool of Lancre sheep, can stand up without feet in them, and can be used to kick down walls in times of incarceration or boredom. He is also known as the kindest and gentlest person around, explicitly because no-one dares to mock him for it.
Zillah from Lost Souls by Poppy Z. Brite is an incredibly badass vampire who impregnates several women throughout the story, who's always described as "beautifully androgynous" with long hair he ties back with a purple scarf.
A Song of Ice and Fire features many examples of this trope. Knights in Westeros pimp out their armor to show off their wealth, often covering themselves in garish colors. Renly Baratheon wears green armor to bring out his eyes, and Loras Tyrell, the Knight of Flowers, covers himself in roses, his house symbol. Thoros of Myr takes the trope literally by wearing his red robes long after they have faded to pink. House Bolton takes the trope to an extreme level. One of their house colors is pink, meant to represent the human skin that they flay from their living enemies. In the Slaver Cities, the warrior caste subvert the trope by wearing ridiculous hairstyles...and leaving the actual fighting to the slaves.
Billy Bright, the leader of the hooligan firm in Football Factory is a florist. Sure it also helps as a front for his drug trafficking.
As a preparatory initiation ordeal he had to parade the principal business streets of Kingsport for a whole day wearing a sunbonnet and a voluminous kitchen apron of gaudily flowered calico. This he did cheerfully, doffing his sunbonnet with courtly grace when he met ladies of his acquaintance. Charlie Sloane, who had not been asked to join the Lambs, told Anne he did not see how Blythe could do it, and HE, for his part, could never humiliate himself so. "Fancy Charlie Sloane in a `caliker' apron and a `sunbunnit,' " giggled Priscilla. "He'd look exactly like his old Grandmother Sloane. Gilbert, now, looked as much like a man in them as in his own proper habiliments."
The YA novel Flipside gives this an interesting spin. The protagonist has spent most of his life as a wallflower, and timidity is built into his basic identity. When in female clothing, however, he no longer feels like himself, so he can adopt any identity he wants—and the identity he wants is an assertive, dominating one. In other words, dresses make him more manly!
According to the novelisation of Iron Man 2, Ivan Vanko likes Nu, Pogodi!, and when he fails to find it in America, gets his cartoon fix from Johnny Test amongst others.
Jay Gatsby from The Great Gatsby, an Oxford graduated high-class and manly man, wears a pink suit. It sends Tom into disbelief.
In Patrick F. McManus's story "The Blue Dress," Rancid Crabtree has his clothes stolen while swimming and is lent a blue dress by a widow to wear while he hunts down the thieves. He tells the kids that all he had to wear when he was in elementary school was a "purty polka dot dress" handed down from his sister Clementine. When asked if he got laughed at for wearing a dress, he answers "only once."
Chris Wohl from Dale Brown's books, a big and fearsome Marine, knows how to look after kids.
In Aaron Allston's Galatea in 2-D, C.J. not only teaches them all guns, he does all the cooking — recruiting Dylan, the only other competent cook as backup.
Finny from A Separate Peace, in one scene, shows up to a school function in a pink shirt and with his school tie as a belt. This only makes him stand out a lot more.
In Vorpal Blade, former Command Master Chief Miller is working as a florist after leaving the US Navy, at least in part chosen because it's a job where he's not going to wind up meeting people that wind up dead. Later he's shown making a floral arrangement to pass the time while aboard the titular spacecraft.
Benjamin Mayhew of the Honor Harrington books is the Protector of the planet of Grayson. He survives an assassination attempt, saving Honor's life in the process, drags his planet through their own version of the Meiji Restoration, and stands as a rock for the commoners to rally behind. His hobby? Flower arrangement (and the hybridization of orchids).
Benet in The Magic Thief is hired muscle for the main character's mentor. He's big, he's quiet, and he's known for glaring angrily at just about everyone. He also makes yummy biscuits (for which there is a recipe included in the back of the book) and knits in his spare time.
Gem from the Dancing Shoes series of books is a preteen boy who does ballet. Except he's not gay and a typical boy his age who is the love interest for the main girl Lucy.
In Dean Koontz's Whispers, one of the side characters is a former drug-dealing Scary Black Man who got out of prison and made a fortune designing dresses and other women's clothing. He mentions that even before he was arrested, his girlfriends always got more compliments when they let him pick their outfits.
A line in A Very Potter Musical become Hilarious in Hindsight when you learn that Quirrell used to press flowers before he snuffed it. Let me remind you this is the same bloke who lived a year with the Dark Lord, a man who does not love and is evil incarnate, sticking of the back of his head. Pressing flowers.
This recently became Ascended Fanon: on Pottermore pressing flowers is listed as one of Quirrell's hobbies.
A minor character in The Heroes of Olympus called Butch, a bulky dude with a shaved head and a face like a pile of bricks. His mother is Iris, the Rainbow Goddess. Got a problem with that?
Thanks to the revelation that Snape is the Half Blood Prince and Hermione's analysis in the book that the handwriting looks more like a girl's than a boy's. Fridge brilliance can now tell us that Snape has girly handwriting.
Aerich in the Dragaera series' "Khaavren Romances" is a stoic, badass warrior who in keeping with the traditions of his "house", is extremely cultured and wears a skirt as part of his battle dress. When not active, he knits for relaxation.
A sailor in The Abandoned is described as "an enormous giant of a man, whiskered like a Highlander, with arms like the branches of oak trees, horny hands with red, bony knuckles, and fingers as big and thick as blood-pudding sausages." He embroiders detailed flowers on linen cloth. When a new sailor ridicules him, Angus punches him out, and the other sailors tell the newbie how foolish he was not because the mockery earns him a blow, but because when the ship docks Angus can take his embroidery to a certain place and get paid handsomely for it.
While Karrin Murphy of The Dresden Files is obviously not male, she works so hard on fitting in with the boys-club CPD that when Harry finally sees her house - and it's adorable - he can't help but comment.
Referenced in the thoughts of Nasuada in Inheritance of Inheritance Cycle, who recalls learning from some of the men in her army who seemingly only had an interest in "women, wine and war" how they have a fondness for memorizing romantic poems, or petting hounds.
Peeta Mellark of The Hunger Games is an amateur wrestler who carries 100 pound bags of flour over his head without a problem, is deadly with a knife and spear, kills big, tough Brutus during the Quarter Quell and whose masculinity is never questioned in the book. He also loves decorating cakes and bakes flower shaped cookies.
My Princess Boy is one of the first children's books for and about little boys who just happen to like frilly princess dresses and sparkling tiaras. Written by Cheryl Kilodavis and illustrated by Suzanne De_Simone, it was inspired by Kilodavis' son Dyson, who at a very early age told his mother "I am a princess boy."
In the Rainbow Magic series, Jack Frost and his goblins like dancing, fashion, and pop stardom, among other things.
Patricia Wrede's Enchanted Forest side-story Utensile Strength has the royal family trying to find the proper wielder for a literal enchanted Frying Pan of Doom. To do this, they hold a "barbarian cook-off", drawing competitors from across the land. Even after the pan's true wielder is found, the barbarians themselves insist on completing the contest.